Am I ugly enough for an Oscar now? 17-plus unsuccessful attempts to de-glamorize movie stars

1. Natalie Portman, Hesher (2011)
Movie stars often have a terrible handicap: They’re too beautiful. While it might make sense for Natalie Portman to play a stripper or a queen, it can be difficult to buy her as an average person. And it’s downright impossible to buy her as a sad sack in mom jeans and giant old-Jewish-man glasses whose greatest ambition in life is to finally work 20 hours a week at a small-town grocery store instead of the 15 she’s currently working. Yet the dour independent drama Hesher has the chutzpah to try to pass Portman off as one of the suffering, homely masses. The de-glamorization process here is spiritual as well as physical. It’s not enough for Portman to look undesirable; she also has to carry an aura of sour, small-time sadness. When Hesher has Portman wonder aloud if she’s simply not attractive enough to score more hours at the grocery store, it practically dares the audience not to scoff in disbelief.

2. Christine Lakin in The Hottie And The Nottie (2008)
Occasionally, the job of de-glamming attractive actors is done so thoroughly it loops back around to the other side, making them so ugly they look less like humans than extras from the Star Wars cantina scene. Consider The Hottie And The Nottie, a misbegotten Paris Hilton bomb that seemed to exist solely to pamper Hilton’s ego. As a child, Hilton’s character had a slightly ugly little friend who grows up to be Christine Lakin beneath warts, moles, stringy hair, bad clothing, and bad teeth that make her look less like an ugly woman than someone trying to pass a college stage-makeup final.

3. Orlando Bloom, Haven (2006)
Imagine you’re Orlando Bloom. You’re rich and famous for playing elves and swashbuckling pirates, but you long for more. You’re an artist, man. You don’t just go to Sundance for the free drinks and parties. You want to create art. So you get a script with a juicy central role: a disfigured, impoverished Cayman Island native stuck in a star-crossed romance with the daughter of a wealthy power-broker. Alas, the 2006 drama Haven, which casts Bloom as the aforementioned townie, betrays the sad fact that no amount of make-up can hide Bloom’s essential dreaminess. He’s a lightweight in dark, murky waters who can’t pull off brooding, intense, or Caymanian. Bloom’s attempt to establish himself as a serious actor here are as admirable as his execution is terrible.

4. Michelle Pfeiffer, Frankie and Johnny (1991)
Terrence McNally’s play Frankie And Johnny In The Clair De Lune is defiantly blue-collar and modest, limiting its action to one set and its cast to two characters. (You can probably guess their names.) It’s a piece about sad, ordinary, not particularly attractive people finding love later in life. This understandably made it a tricky proposition for Hollywood, which likes its lovers sexy and young. So Happy Days guru Garry Marshall came onboard and transformed a blue-collar play into a properly glossy Hollywood movie with proper glossy Hollywood movie stars. Al Pacino can almost get away with playing an ordinary man. Michelle Pfeiffer, on the other hand, is simply too beautiful to convince as a woman who has to serve food and wait tables. Stick her in sneakers and a practical skirt and she still looks like a goddess.

5. Jessica Biel, Home Of The Brave (2006)
The hilariously misconceived Iraq War drama Home Of the Brave does everything it conceivably can to make Jessica Biel look like something other than a sex bomb. The film gives her a non-glamorous job as the world’s only heterosexual female gym teacher, tries to hide her famous curves underneath unflattering outfits, and supplies her Iraq War veteran character with a hook for a hand and a mind full of traumatic memories. Like all of the films in this Inventory, however, Home Of The Brave makes the crucial mistake of trying way too hard. Irwin Winkler’s film is so laden with melodrama and missteps that Biel’s flagrant miscasting doesn’t register anywhere near the top of the list of its offenses: When a film contains lines like, “It only takes one good hand to push people away,” its problems go much deeper.

6. Lindsay Lohan, I Know Who Killed Me (2007)
The filmmakers behind the 2007 thriller I Know Who Killed Me had the unenviable task of trying to de-glam Lindsay Lohan for two different roles in the same film. Lohan plays Aubrey Fleming, a regular high-school student who aspires to be a writer, as well as stripper Dakota Moss, who happens to share her name with a character from one of Aubrey’s short stories. The plot is muddled and full of twists and turns involving mistaken identity, stigmata twins, a serial killer, and dark family secrets—bad enough to earn the film an auspicious nine Razzie nominations. It came at a time when Lohan was attempting to make the transition from Disney tween star to more serious, adult fare like Bobby and Chapter 27—the same time her enjoyment of the celebrity lifestyle was splashed across gossip magazines and websites. Neither glasses nor dark hair dye could distract viewers from the fact that they were watching Lindsay Lohan, socialite. It was easier to ask moviegoers to accept the film’s implausible plot twists than to buy Lohan as your average high school student or a mysterious stripper found on the side of the road, dual roles for which she won two Razzie awards.

7. Jared Leto, Chapter 27 (2008)
The negligible buzz over the hilariously overwrought Mark David Chapman biopic Chapter 27 revolved around star Jared Leto’s massive weight gain. Leto guzzled olive oil and chocolate milkshakes for months to prepare physically for the role of a fat, sad, melodramatic loner staring down a dark destiny. But his effort was for naught: For all of his furious overacting and excess verbiage, the My So Called Life pretty boy never comes off as anything other than a hunky actor in a fat suit desperately trying to crawl inside the skin of someone he doesn’t understand.

8. Jason Schwartzman, Spun (2003)
Jason Schwartzman is fated to exist forever in the shadow of his lead performance as the world’s most precocious dilettante in Rushmore. The 2003 black comedy Spun coats Schwartzman in multiple layers of grime and has his desperate, speed-addicted character do things like handcuff and duct-tape a woman’s mouth after having drug-fueled sex with her. But no matter how abominably Schwartzman’s character behaves, the ghost of Max Fischer remains. You can’t help but wanted to pinch his cheek or playfully run your fingers through his hair.

9. Bradley Cooper, Limitless (2011)
The entertaining wish-fulfillment thriller Limitless asks audiences to believe a pill can harness the full power of their brains, but asking them to buy Bradley Cooper as a burnout science-fiction writer is even more far-fetched. Maybe that’s why he’s only a long-haired, unshaven slacker for about 10 minutes at the beginning of the film. The rest of the time, he isn’t hiding his movie-star DNA under stubble and shabby clothes. He’s the Bradley Cooper we’ve come to know through Wedding Crashers and The Hangover: handsome, confident, and kind of douchey.

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10. Kate Winslet, Little Children (2006)
Kate Winslet is sexy, whether she’s modeling for a Leonardo DiCaprio sketch or hiding a horrible Holocaust secret while sitting, illiterate, in a bathtub. And she’s certainly sexy in spite of her attempts to portray a dowdy housewife in the frequently unsexy 2006 film Little Children. Her voice and mannerisms are supposed to convey a sense of unease, and though she’s an excellent actress—she was nominated for the big one at the Oscars that year—her glamour and beauty burst through.

11. Uma Thurman, My Super Ex-Girlfriend (2006)
In the horrifically misconceived superhero romantic comedy My Super Ex-Girlfriend, Uma Thurman is unconvincing as both a sexy superhero and a mousy librarian type with nerd-rage issues. The film gets it backwards: Thurman doesn’t look as hot as she should be in superhero garb and nowhere near as unattractive as she’s supposed to be as a normal person. Blame it on Thurman’s tall, model-skinny body. She simply can’t pass as normal and should probably stop trying to do so.

12. Rachael Leigh Cook, She’s All That (1999)
It’s like the hair, makeup, and wardrobe stylists on She’s All That didn’t even try when it came to de-glamming pretty, petite Rachael Leigh Cook for She’s All That, a 1999 take on Pygmalion. Typically, the makeover in “nottie-to-hottie” movies involves the ceremonial removal of glasses. However, Cook looks just as (if not more) beautiful with her glasses on, as the moody artist, than off, as the made-over object of Freddie Prinze, Jr.’s affection. Sure, she sometimes dresses a little unusually by 1999 high-school standards (and her being a performance artist is, like, totally weird), but in the end, many women would probably endure a makeover just to look like pre-makeover Laney Boggs.

13. Keanu Reeves, The Watcher (2000)
As befits a man whose first name means “Breeze,” Keanu Reeves has a soothing, almost sleep-inducingly gentle presence: He’s pretty like a girl and speaks in a perpetually bored-sounding monotone. Yet when the makers of The Watcher looked at Reeves’ delicate features and beautiful hair, they saw a deranged serial killer intent on antagonizing the FBI agent hunting him down, played by James Spader. That’s right: James Spader and Keanu Reeves made a movie together where Spader is the good guy and Reeves is the murderous creep. Yet the public somehow found the switcheroo unconvincing. Strange.

14. Jennifer Aniston, Just Go With It (2011)
In romantic comedies involving serious makeovers, the girl who’s inevitably going to end up with the guy at the end can never be too ugly because, well, it’s a romantic comedy and not a soul-searing look at the dark life of a truck-stop prostitute in Nebraska or something. This has the unintended effect of making the hero seem like even more of an idiotic jackass than usual. Case in point: Just Go With It, in which Adam Sandler, no stranger to playing idiotic jackasses, gets so hung up on Brooklyn Decker that he concocts an elaborate scheme to continue getting in her pants when she finds the fake wedding ring he wears to score with hot chicks and assumes he’s married. Enter his mousy co-worker, a woman with two kids whom he’s taken for granted all these years, but someone he now needs to put on a slinky dress and look terrific. Good thing that his co-worker is Jennifer Aniston instead of Marge from Accounting. It’s as though the producers didn’t even try, stepping back from Aniston and considering her from all angles, holding out their hands like picture frames toward her and saying, “Well, what if we did… nah!” before ultimately just slapping a pair of glasses on her.

15. Nicole Kidman, The Human Stain (2003)
In his novel The Human Stain, Philip Roth described the illiterate, battered janitor his 65-year-old protagonist takes to bed as “not the enticing siren who takes your breath away but a clean-cut-looking woman about whom one thinks, As a child she must have been very beautiful.” Which is why it’s hard to believe that for the 2003 film version, director Robert Benton cast Nicole Kidman, at the time the go-to film star for playing enticing sirens who leave men breathless. No matter how she slouches or wears bulky sweaters, regardless of her tasteful tattoo and mousy-colored (but oh-so-carefully tousled and styled) hair, Kidman is still astoundingly gorgeous, and she plays her role more like a slithering, smoky ’40s femme fatale than a coarse, damaged working-class woman fighting for a little pleasure. It’s impossible to believe that she’s been eking out a living as a janitor in a New England town; her role as the most in-demand courtesan at the Moulin Rouge is just a change of clothing away.

16. Mel Gibson, The Man Without a Face (1993)
While still at the height of his handsomeness—and shortly after winning a shitload of MTV Movie Awards for Lethal Weapon 3—Mel Gibson decided to get serious with The Man Without A Face, which he both starred in and directed. Gibson plays a man disfigured in a car accident, but conveniently disfigured so that exactly half of his face is still super-duper handsome. What are the chances that the film’s financiers required that at least some of Gibson’s handsomeness be left intact? Some might consider Gibson’s decision to get ugly brave, but it would have been braver if he’d left intact the pedophilia elements from the novel.

17-plus. Emma Stone, Kat Dennings, Katharine McPhee, Rumer Willis, and all the rest of Zeta Alpha Zeta, The House Bunny (2008)
The plot of The House Bunny isn’t rocket science. An ex-Playboy bunny, played by Anna Faris, gets a job as a house mother of a struggling sorority with a not-so-cool reputation. As members of ZAZ, Stone, Dennings, and the others are diamonds in the rough, in that they wear huge T-shirts, glasses, boyish haircuts, and in Willis’ unfortunate case, a massive back brace. Faris’ character gives them a centerfold-style makeover, and all of a sudden they’re the toast of campus, dorky laughs and all. It’s Revenge Of The Nerds redux, but, like, totally sexier. Thing is, even when Emma Stone and Kat Dennings are in unflattering garb and stupid haircuts, they’re still Emma Stone and Kat Dennings. Throwing baby tees, push-up bras, and mascara on them is just gilding the lily.

Don’t miss the companion Inventory: I am ugly enough for an Oscar now! 16 successfully de-glamorized movie stars.